Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

Max von Delius; Edzard M. Geertsema; David A. Leigh; Alexandra M. Z. Slawin

doi:10.1039/c0ob00214c

Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

Max von Delius, Edzard M. Geertsema, David A. Leigh, Alexandra M. Z. Slawin

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis and characterisation, including solid state structure, of a macrocycle containing both a hydrazone and a disulfide linkage is described. Selective ring-opening of the macrocycle under thermodynamic control could be achieved at either the disulfide or the hydrazone linkage by applying mutually exclusive sets of reaction conditions.

Original language	English
Pages (from-to)	4617-4624
Number of pages	8
Journal	Organic Electronics
Volume	8
Issue number	20
DOIs	https://doi.org/10.1039/c0ob00214c
Publication status	Published - 2010

Keywords

COMBINATORIAL LIBRARIES
SYSTEMS CHEMISTRY
EXCHANGE
INTERPLAY
KINETICS

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10.1039/c0ob00214c

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title = "Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions",

abstract = "The synthesis and characterisation, including solid state structure, of a macrocycle containing both a hydrazone and a disulfide linkage is described. Selective ring-opening of the macrocycle under thermodynamic control could be achieved at either the disulfide or the hydrazone linkage by applying mutually exclusive sets of reaction conditions.",

keywords = "COMBINATORIAL LIBRARIES, SYSTEMS CHEMISTRY, EXCHANGE, INTERPLAY, KINETICS",

author = "{von Delius}, Max and Geertsema, {Edzard M.} and Leigh, {David A.} and Slawin, {Alexandra M. Z.}",

year = "2010",

doi = "10.1039/c0ob00214c",

language = "English",

volume = "8",

pages = "4617--4624",

journal = "Organic Electronics",

issn = "1566-1199",

publisher = "Elsevier",

number = "20",

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TY - JOUR

T1 - Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

AU - von Delius, Max

AU - Geertsema, Edzard M.

AU - Leigh, David A.

AU - Slawin, Alexandra M. Z.

PY - 2010

Y1 - 2010

N2 - The synthesis and characterisation, including solid state structure, of a macrocycle containing both a hydrazone and a disulfide linkage is described. Selective ring-opening of the macrocycle under thermodynamic control could be achieved at either the disulfide or the hydrazone linkage by applying mutually exclusive sets of reaction conditions.

AB - The synthesis and characterisation, including solid state structure, of a macrocycle containing both a hydrazone and a disulfide linkage is described. Selective ring-opening of the macrocycle under thermodynamic control could be achieved at either the disulfide or the hydrazone linkage by applying mutually exclusive sets of reaction conditions.

KW - COMBINATORIAL LIBRARIES

KW - SYSTEMS CHEMISTRY

KW - EXCHANGE

KW - INTERPLAY

KW - KINETICS

U2 - 10.1039/c0ob00214c

DO - 10.1039/c0ob00214c

M3 - Article

SN - 1566-1199

VL - 8

SP - 4617

EP - 4624

JO - Organic Electronics

JF - Organic Electronics

IS - 20

ER -

Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions

Abstract

Keywords

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